Reaction #833532

Reaction equation

acryloyl chloride

cyclopentadiene

acryloyl chloride

→

norbornene-5-carbonylchloride

Conditions

Workup

1. 1
   Otherdigital thermometer, glass stopper, an addition funnel with a nitrogen gas purge
2. 2
   workup.ADDITIONwas added drop
3. 3
   Otherwise to the reaction over about three hours
4. 4
   Temperaturewhile maintaining the reaction temperature between 0-10° C
5. 5
   Otherthe cooling bath was removed
6. 6
   Temperatureto warm to room temperature overnight
7. 7
   workup.DISTILLATIONThe reaction mixture was distilled under vacuum
8. 8
   Othercollecting 533 g of the title product
9. 9
   workup.DISTILLATIONdistilling at 54-56° C. at a pressure of 300 milliTorr

Procedure

A 1-L, three-neck round-bottom flask equipped with a magnetic stirrer, digital thermometer, glass stopper, an addition funnel with a nitrogen gas purge, and a dry-ice cooling bath was charged with freshly distilled cyclopentadiene (248 g, 3.75 mol), which was cooled to 0° C. The addition funnel was charged with freshly distilled acryloyl chloride (317 g, 3.5 mol), which was added drop wise to the reaction over about three hours while maintaining the reaction temperature between 0-10° C. After the acryloyl chloride addition was complete, the cooling bath was removed and the reaction allowed to warm to room temperature overnight. The reaction mixture was distilled under vacuum, collecting 533 g of the title product distilling at 54-56° C. at a pressure of 300 milliTorr.

Source